- The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry
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Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.
- Somei,Yamada,Kurauchi,Nagahama,Hasegawa,Yamada,Teranishi,Sato,Kaneko
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- The first total synthesis of bufobutanoic acid by two routes based on nucleophilic substitution reaction on indole nucleus
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Regioselective nucleophilic substitution reaction of 1- hydroxytryptamines led to establish two novel routes for the first synthesis of bufobutanoic acid. An effective synthesis of 5-benzyloxytryptamine from tryptamine is also reported.
- Kurauchi, Takashi,Nagahama, Yoshiyuki,Hasegawa, Masakazu,Yamada, Koji,Somei, Masanori
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p. 1017 - 1019
(2007/10/03)
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